تفاعل #539722

معادلة التفاعل

[(2-amino-5-chloro-benzyl)-tert-butoxycarbonyl-amino]-acetic acid ethyl ester

potassium tert-butoxide

water

ammonium chloride

→

title compound

المردود 88.0%

7-Chloro-2-oxo-1,2,3,5-tetrahydro-benzo[1,4]diazepine-4-carboxylic acid tert-butyl ester

المردود 88.0%

المذيبات

tetrahydrofuran

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONaddition the cooling bath
2. 2
   أخرىwas removed
3. 3
   أخرىreaction mixture
4. 4
   ترشيحAfter 10 minutes the precipitate was collected by filtration
5. 5
   أخرىThe layers were separated from the filtrate
6. 6
   تجفيفdried over anhydrous sodium sulfate
7. 7
   تركيزconcentrated in vacuo
8. 8
   ترشيحhad previously been collected by filtration
9. 9
   أخرىcrystallized from hot ethyl acetate

الإجراء التجريبي

To a solution of [(2-amino-5-chloro-benzyl)-tert-butoxycarbonyl-amino]-acetic acid ethyl ester (60 g, 0.18 mol) in tetrahydrofuran (600 ml) was added potassium tert-butoxide (22 g, 0.19 mol) in small portions at 5° C. under cooling on an ice-water batch. After completed addition the cooling bath was removed and reaction mixture was stirred for 3 h at room temperature followed by addition of water (400 ml), saturated aqueous ammonium chloride solution (280 ml) and ethyl acetate (800 ml). After 10 minutes the precipitate was collected by filtration. The layers were separated from the filtrate, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was combined with the precipitate, which had previously been collected by filtration, and crystallized from hot ethyl acetate to give the title compound (46 g, 88%) as white solid. MS m/e: 295 (M−H+).

المصدر